US4153801A - Polyethers having terminal amino groups - Google Patents

Polyethers having terminal amino groups Download PDF

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Publication number
US4153801A
US4153801A US05/735,281 US73528176A US4153801A US 4153801 A US4153801 A US 4153801A US 73528176 A US73528176 A US 73528176A US 4153801 A US4153801 A US 4153801A
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US
United States
Prior art keywords
formula
mol
compound according
ether
polyalkylene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US05/735,281
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English (en)
Inventor
Oskar Schmidt
Walter Sibral
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Lim Holding SA
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Lim Holding SA
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Filing date
Publication date
Priority claimed from AT814975A external-priority patent/AT341784B/de
Priority claimed from AT815475A external-priority patent/AT341786B/de
Priority claimed from AT815375A external-priority patent/AT340689B/de
Priority claimed from AT815275A external-priority patent/AT340688B/de
Application filed by Lim Holding SA filed Critical Lim Holding SA
Application granted granted Critical
Publication of US4153801A publication Critical patent/US4153801A/en
Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5054—Polyethers having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
    • C08G18/506—Polyethers having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing two nitrogen atoms in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/52—Polythioethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen

Definitions

  • polyureas possess a number of considerable advantages over polyurethanes of corresponding structure.
  • Polyureas are obtained by reaction of polyisocyanates with polyamines. Suitable polyamines are particularly polyether polyamines of higher molecular weight. According to German Offenlegungsschrift No. 2 019 432, polyamines suitable for the production of such polyureas are obtained from aliphatic polyether polyols and isatic acid anhydride.
  • a further object of the invention is to provide a process for the production of these compounds.
  • the production of the compounds of the present invention is advantageously effected by heating of a compound of the general formula (HX) z R (general formula III) wherein z is 2 or 3 and R and X have the meaning defined above with at least z equivalents of isatic acid anhydride in the presence of strong bases to temperatures of 30° to 150° C., perferably to temperatures of 45° to 130° C.
  • the reaction can be carried out with or without the presence of inert solvents.
  • the amount of catalyst used can be varied within a wide range. Preferably, 1 to 10 parts by weight of the alkaline compound per 100 parts by weight of isatic acid anhydride are employed.
  • the reaction is completed as soon as gas development ceases.
  • the catalyst and excess isatic acid anhydride are filtered off, optionally after addition of an inert solvent, and the final product is obtained with a high degree of purity after treatment with CO 2 , shaking with water and drying in vacuo under stirring.
  • simple filtration of the amino polyether under pressure suffices.
  • Suitable starting materials for the process according to the invention are polyether diols and polyether triols as well as polythioether dithiols and polythioether triols and diols, triols, dithiols and trithiols comprising polyether segments or polythioether segments.
  • Preferred in the process according to the invention is the use of polymerisates of the formula III which are obtained by reacting ethylene oxide or propylene oxide or other 1,2-alkylene oxides or ethylene oxide and propylene oxide with a compound corresponding to R in formula II wherein B is hydrogen, CH 2 CH 2 OH or CH 2 CH(CH 3 )OH.
  • m, n and o in each case represent such integers that molecular weights of about 500 to about 15000, preferably of about 500 to about 3000 (when using diols or dithiols) and of about 800 to about 15000 (when employing triols or trithiols) are obtained in the compounds of the formula I.
  • A stands for an alkylidene group of 1 to 6 carbon atoms.
  • Particularly obtainable among these are compounds of the formula I wherein A represents an isopropylidene group, an ethylidene group or a methyl vinylene group.
  • B in the formula I can have the meaning of a polyethylene ether group, a polypropylene ether group or a polyalkylene ether group comprising ethylene ether groups and propylene ether groups in any given sequence.
  • the polyalkylene ether group can further contain ether groups as well as thioether groups.
  • B stands for a polyalkylene ether group derived from tetrahydrofurane, a polyalkylene ether group containing ethylene ether groups and alkylene ether groups derived from tetrahydrofurane in any given sequence or for a polyalkylene ether group containing alkylene ether groups derived from tetrahydrofurane and propylene ether groups, in any given sequence.
  • a further object of the present invention is the use or application of the compounds according to the invention or obtainable according to the process of the invention as reactants with polyisocyanate in the production of plastic materials according to the isocyanate polyaddition process.
  • plastic materials from the new compounds according to the invention in the isocyanate polyaddition process can be effected in any given manner conventional in polyurethane chemistry, i.e. employed in the reaction of polyhydroxyl compounds with polyisocyanates.
  • reaction of the new compounds with polyisocyanates can be carried out in the presence of all the additives known in polyurethane chemistry, such as catalysts, flame-retarding substances and the like.
  • the polyadducts have preferably been obtained up to now in the presence of low molecular aromatic diamines as chain extenders. Since these diamines are carcinogenic, their use is encountering objections of a physiological nature.
  • the use of low molecular aromatic diamines can be completely omitted in the production of elastomeric plastic materials of high modulus of elasticity.
  • Suitable polyisocyanates for the production of polyadducts employing the new compounds of the present invention are all polyisocyanates known in polyurethane chemistry, such as, for instance, tetramethylene diisocyanate, hexamethylene diisocyanate, 2,4-diisocyanatotoluene, 2,6-diisocyanatotoluene, mixtures of these isomers, 4,4-diisocyanato diphenyl methane or the like.
  • the polyadducts produced employing the new compounds according to the invention possess considerable advantages over polyurethanes of corresponding structure, particularly due to the increase in elasticity, stability and thermal stability.
  • Example 15 188.4 g (0.2 mol) of the diamine produced according to Example 2 and 37 g of the toluylene diisocyanate used in Example 15 are heated in a mould first for 30 minutes to 60° C. and then for 24 hours to 100° C. This yields an elastomer of excellent mechanical properties.
  • the tensile strengths of the elastomers produced according to Examples 18 to 22 ranged from 280 to 350 kp cm -2 , the structural strengths from 50 to 85 kp cm -1 and the Shore hardnesses (DIN 53 505) from 58 to 96.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polyethers (AREA)
US05/735,281 1975-10-27 1976-10-26 Polyethers having terminal amino groups Expired - Lifetime US4153801A (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
AT814975A AT341784B (de) 1975-10-27 1975-10-27 Verfahren zur herstellung von neuen, endstandige aminogruppen aufweisenden polyathern und die herstellung von kunststoffen hieraus
AT8153/75 1975-10-27
AT8152/75 1975-10-27
AT815475A AT341786B (de) 1975-10-27 1975-10-27 Verfahren zur herstellung von neuen, endstandige aminogruppen aufweisenden polyathern und die herstellung von kunststoffen hieraus
AT8149/75 1975-10-27
AT815375A AT340689B (de) 1975-10-27 1975-10-27 Verfahren zur herstellung von neuen, endstandige aminogruppen aufweisenden polyathern und ihre verwendung als reaktionspartner bei der herstellung von kunststoffen
AT815275A AT340688B (de) 1975-10-27 1975-10-27 Verfahren zur herstellung von neuen, endstandige aminogruppen aufweisenden polyathern und ihre verwendung als reaktionspartner bei der herstellung von kunststoffen
AT8154/75 1975-10-27

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US06009640 Division 1979-02-05

Publications (1)

Publication Number Publication Date
US4153801A true US4153801A (en) 1979-05-08

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ID=27422248

Family Applications (1)

Application Number Title Priority Date Filing Date
US05/735,281 Expired - Lifetime US4153801A (en) 1975-10-27 1976-10-26 Polyethers having terminal amino groups

Country Status (14)

Country Link
US (1) US4153801A (ko)
JP (1) JPS5268296A (ko)
AU (1) AU507217B2 (ko)
BE (1) BE847681A (ko)
BR (1) BR7607242A (ko)
CA (1) CA1080227A (ko)
DD (1) DD127235A5 (ko)
DE (1) DE2648825C2 (ko)
ES (1) ES453218A1 (ko)
FR (1) FR2347352A1 (ko)
GB (1) GB1540153A (ko)
IT (1) IT1124721B (ko)
NL (1) NL7611907A (ko)
SE (1) SE7611938L (ko)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4229561A (en) * 1979-04-13 1980-10-21 Lim-Holding, S.A. Polyurea polymer prepared from polyethers having heterocyclic groups and terminal amino groups
US4260729A (en) * 1980-01-03 1981-04-07 Lim-Holding S.A. Polyurea polymers formed from polyethers having terminal amino groups
US4283548A (en) * 1979-04-10 1981-08-11 Lim-Holding S.A Diisatoic acid or triisatoic acid derivatives
US4328322A (en) * 1979-12-03 1982-05-04 Polaroid Corporation Synthetic polymers by polyisocyanate polyaddition process
US4472568A (en) * 1981-11-12 1984-09-18 Bayer Aktiengesellschaft Process for the preparation of polyamines from N-monoaryl-N',N'-dialkyl urea compounds and their use for the synthesis of polyurethanes
US4501873A (en) * 1982-12-04 1985-02-26 Bayer Aktiengesellschaft Preparation of polyamines by hydrolyzing a polyisocyanate in the presence of an isocyanate-reactive compound with water
US4515923A (en) * 1982-06-23 1985-05-07 Bayer Aktiengesellschaft Polyamines and a process for their production
US4525534A (en) * 1982-07-21 1985-06-25 Bayer Aktiengesellschaft Polyamines and a single-stage process for the production thereof
US4540720A (en) * 1981-08-07 1985-09-10 Bayer Aktiengesellschaft Polyamines, a process for the production of polyamines and their use in the production of polyurethanes
US4565645A (en) * 1982-06-23 1986-01-21 Bayer Aktiengesellschaft Single-stage process for the production of polyamines and polyamines produced by such process
US4723032A (en) * 1981-11-12 1988-02-02 Bayer Aktiengesellschaft Modified polyamines and a process for their production
US4724252A (en) * 1985-08-27 1988-02-09 Bayer Akitengesellschaft Polyamines and a process for their production from polyisocyanates
US4931595A (en) * 1985-10-01 1990-06-05 Bayer Aktiengesellschaft Catalytic hydrolysis process for polyamines
US4970342A (en) * 1982-06-23 1990-11-13 Bayer Aktiengesellschaft Polyamines and a process for the production thereof
US5283364A (en) * 1985-10-18 1994-02-01 Bayer Aktiengesellschaft Hydrolysis process for polyamines
US5510535A (en) * 1994-11-22 1996-04-23 Bayer Corporation Ether-linked amine-terminated polyethers and a process for their production

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4229576A (en) 1977-12-09 1980-10-21 Ciba-Geigy Corporation Anthranilates of oxyalkylated cyanuric acid
US4202987A (en) 1977-12-09 1980-05-13 Ciba-Geigy Corporation Bis-anthranilates
US4191835A (en) * 1978-04-27 1980-03-04 Ciba-Geigy Corporation Bis-anthranilates of urea derivatives
US4191836A (en) * 1978-04-27 1980-03-04 Ciba-Geigy Corporation Anthranilates of polyoxyethylated carboxylic acid
US4847416A (en) * 1986-10-27 1989-07-11 The Dow Chemical Company Capping of polyols with aromatic amines

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3787405A (en) * 1970-11-18 1974-01-22 Ciba Geigy Ag Diglycidyl compounds containing a n-heterocyclic ring
US3984606A (en) * 1974-04-15 1976-10-05 W. R. Grace & Co. Curable polyene-polythiol hydantoin coating compositions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1812003A1 (de) * 1968-11-30 1970-06-18 Bayer Ag Hydantoine mit alkoholischen OH-Gruppen
DE2245345A1 (de) * 1972-09-15 1974-03-21 Bayer Ag Hydantoinringe enthaltende polyaetherurethane und deren verwendung als antistatika

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3787405A (en) * 1970-11-18 1974-01-22 Ciba Geigy Ag Diglycidyl compounds containing a n-heterocyclic ring
US3984606A (en) * 1974-04-15 1976-10-05 W. R. Grace & Co. Curable polyene-polythiol hydantoin coating compositions

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4283548A (en) * 1979-04-10 1981-08-11 Lim-Holding S.A Diisatoic acid or triisatoic acid derivatives
US4229561A (en) * 1979-04-13 1980-10-21 Lim-Holding, S.A. Polyurea polymer prepared from polyethers having heterocyclic groups and terminal amino groups
US4328322A (en) * 1979-12-03 1982-05-04 Polaroid Corporation Synthetic polymers by polyisocyanate polyaddition process
US4260729A (en) * 1980-01-03 1981-04-07 Lim-Holding S.A. Polyurea polymers formed from polyethers having terminal amino groups
USRE32677E (en) * 1981-08-07 1988-05-24 Bayer Aktiengesellschaft Polyamines, a process for the production of polyamines and their use in the production of polyurethanes
US4540720A (en) * 1981-08-07 1985-09-10 Bayer Aktiengesellschaft Polyamines, a process for the production of polyamines and their use in the production of polyurethanes
US4472568A (en) * 1981-11-12 1984-09-18 Bayer Aktiengesellschaft Process for the preparation of polyamines from N-monoaryl-N',N'-dialkyl urea compounds and their use for the synthesis of polyurethanes
US4723032A (en) * 1981-11-12 1988-02-02 Bayer Aktiengesellschaft Modified polyamines and a process for their production
US4970342A (en) * 1982-06-23 1990-11-13 Bayer Aktiengesellschaft Polyamines and a process for the production thereof
US4565645A (en) * 1982-06-23 1986-01-21 Bayer Aktiengesellschaft Single-stage process for the production of polyamines and polyamines produced by such process
US4515923A (en) * 1982-06-23 1985-05-07 Bayer Aktiengesellschaft Polyamines and a process for their production
US4525534A (en) * 1982-07-21 1985-06-25 Bayer Aktiengesellschaft Polyamines and a single-stage process for the production thereof
US4501873A (en) * 1982-12-04 1985-02-26 Bayer Aktiengesellschaft Preparation of polyamines by hydrolyzing a polyisocyanate in the presence of an isocyanate-reactive compound with water
US4724252A (en) * 1985-08-27 1988-02-09 Bayer Akitengesellschaft Polyamines and a process for their production from polyisocyanates
US4931595A (en) * 1985-10-01 1990-06-05 Bayer Aktiengesellschaft Catalytic hydrolysis process for polyamines
US5283364A (en) * 1985-10-18 1994-02-01 Bayer Aktiengesellschaft Hydrolysis process for polyamines
US5510535A (en) * 1994-11-22 1996-04-23 Bayer Corporation Ether-linked amine-terminated polyethers and a process for their production
US5763667A (en) * 1994-11-22 1998-06-09 Bayer Corporation Ether-linked amine-terminated polyethers and a process for their production

Also Published As

Publication number Publication date
SE7611938L (sv) 1977-04-28
DE2648825A1 (de) 1977-04-28
FR2347352A1 (fr) 1977-11-04
NL7611907A (nl) 1977-04-29
GB1540153A (en) 1979-02-07
DD127235A5 (ko) 1977-09-14
CA1080227A (en) 1980-06-24
BE847681A (fr) 1977-02-14
JPS5268296A (en) 1977-06-06
IT1124721B (it) 1986-05-14
DE2648825C2 (de) 1983-06-01
BR7607242A (pt) 1977-09-13
FR2347352B1 (ko) 1982-10-08
AU1901876A (en) 1978-05-04
AU507217B2 (en) 1980-02-07
ES453218A1 (es) 1978-05-01

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